4. Rainwater's Oil Bet

By Justin FoxMonday, Nov. 03, 2008

Pat Sullivan / AP

Investor Richard Rainwater sells his billions of dollars in oil company shares in May, when the price of oil hits $129 a barrel. In September, he starts buying again with the price at $90 a barrel. No, he doesn't get the timing exactly right  oil subsequently dropped below $50 a barrel. But would you really want to bet against the proposition that oil prices are headed higher in the long run?